CN111978335B - Narrow-bandgap organic acceptor photovoltaic material with divinyl pi-bridge and preparation method and application thereof - Google Patents
Narrow-bandgap organic acceptor photovoltaic material with divinyl pi-bridge and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a preparation method and application of a narrow-bandgap organic acceptor photovoltaic material with a divinyl pi-bridge. The structural formula of the narrow-bandgap organic receptor photovoltaic material provided by the invention is shown as a formula I. DA 'D in the formula I is an aromatic fused ring unit, A is an electron-deficient terminal unit, and the DA' D fused ring unit is connected with the A unit through a divinyl pi-bridge. The material has strong absorption in a near infrared region, has proper electronic energy level and better electronic transmission performance, and can be used as an electron acceptor material to be applied to organic solar cells and optical detector devices.
Description
Technical Field
The invention belongs to the field of organic photoelectric materials, and particularly relates to a narrow-bandgap organic receptor photovoltaic material with a divinyl pi-bridge and application thereof in an organic solar cell and a light detection device.
Background
With the increasing prominence of energy crisis and environmental problems, the search for reliable clean energy becomes an urgent global problem, and the development and utilization of solar energy will be an effective method for dealing with the energy crisis. Among the numerous solar cell devices, organic solar cells have advantages of solution-processibility, flexibility, and translucency [ li never boat, acc. Particularly, the rapid development of the A-D-A class [ adv.Mater.,2015,27(7): 1170-. In the solar spectrum, a large part of energy is distributed in the near infrared region, and most of current receptor materials are not high in absorption and utilization efficiency in the region, so that the synthesis of the narrow-bandgap receptor photovoltaic material with good photoelectric performance is important for the field of organic solar cells.
A common method for reducing the optical band gap of acceptor Materials is to enhance the electron donating ability of the middle fused ring nucleus and the electron withdrawing ability of the terminal acceptor unit, thereby enhancing the charge transfer within the molecule to achieve red-shifting of the absorption spectrum [ Nature Reviews Materials,2018,3(3):1-19 ]. Meanwhile, the introduction of conjugated pi-bridges between the fused-ring core units and the terminal acceptor units can expand the conjugation length of the molecules, and is also an effective method for reducing the band gap of the molecules [ Advanced Materials,2016,28(37):8283-8287 ]. However, currently, there are still few efficient narrow bandgap organic photovoltaic materials (especially acceptor materials with absorption sidebands exceeding 1000 nm).
Disclosure of Invention
Aiming at the problems of narrow absorption range, unsatisfactory photoelectric performance and the like of a small molecule receptor photovoltaic material in the existing organic solar cell, the invention provides a molecular design strategy of inserting a double-bond pi bridge between a middle DA' D fused ring nucleus unit and a terminal receptor unit of a receptor, wherein the introduction of the double-bond pi bridge can expand the conjugation length of molecules, increase electron delocalization, remarkably increase charge transfer in the molecules and reduce the optical band gap of the molecules.
The invention aims to provide a narrow bandgap organic acceptor photovoltaic material with divinyl pi-bridge.
The structural formula of the narrow-bandgap organic acceptor photovoltaic material with the divinyl pi-bridge is shown as a formula I:
in the formula I, the DA' D condensed ring group is selected from any one of the following formulas II-1 to II-4:
r in the formulas II-1, II-3 and II-41Any one selected from the following groups: alkyl, alkoxy, alkylthio, silyl, acyl, acyloxy, acylthio, ester, amino, amide. The alkyl group contained in each of the above groups is a linear or branched alkyl group having 1 to 12 carbon atoms.
In the formula II-2, R1，R2The same or different, each is selected from any one of the following groups: alkyl, alkoxy, alkylthio, silyl, acyl, acyloxy, acylthio, ester, amino, amide. The alkyl group contained in each group is a linear or branched alkyl group having 1 to 12 carbon atoms;
the Ar group in the formulas II-1 to II-4 is connected with A ' (A ' in DA ' D) in a condensed mode, Ar is a conjugated aromatic ring or a condensed ring formed by the conjugated aromatic ring, and can be any one of the following groups: a thiophene group, a thiophene derivative group, a bithiophene derivative group, a pyrrolodithienyl derivative group; the details are as follows:
wherein R is3Any one selected from the following groups: hydrogen atom, alkyl of C1-C12, and alkoxy of C1-C12.
In the formula I, the group A is selected from any one of the following structural formulas:
wherein R is4Any one selected from the following groups: H. f, Cl, Br, I, alkyl, cycloalkyl, alkoxy, alkylthio, ester group and carbonyl; wherein the alkyl, the alkoxy and the alkylthio are all straight-chain or branched alkyl groups with 1-6 carbon atoms; the cycloalkyl is C3-C12.
The narrow bandgap organic acceptor photovoltaic material with divinyl pi-bridge provided by the invention can be specifically, but not limited to, the following structure:
the invention provides a preparation method of a divinyl pi-bridge-containing narrow-bandgap organic acceptor photovoltaic material shown in a formula I, which comprises the following steps:
1) under the protection of inert gas, the compound shown in the formula A, tributyl (1, 3-dioxane-2-ylmethyl) phosphorus bromide and sodium hydride are subjected to a phosphorus ylide reaction to obtain a compound shown in the formula B:
2) and (3) carrying out a Knoevenagel reaction on the compound shown in the formula B and the receptor unit A to obtain the compound shown in the formula I.
Wherein the acceptor unit A is selected from any one of the following:
wherein R is4Is selected fromAny one of the following groups: H. f, Cl, Br, I, alkyl, cycloalkyl, alkoxy, alkylthio, ester group and carbonyl; wherein the alkyl, the alkoxy and the alkylthio are all straight-chain or branched alkyl groups with 1-6 carbon atoms; the cycloalkyl is C3-C12.
In step 1) of the method, the conditions of the phosphorus ylide reaction are as follows: the solvent is ultra-dry tetrahydrofuran, the adding amount of tributyl (1, 3-dioxane-2-ylmethyl) phosphorus bromide and sodium hydride is 2-5 times of the molar amount of the compound shown in the formula A, the mixture is stirred for 12-36 hours at normal temperature, and after the reaction is finished, the redundant sodium hydride is quenched by 5% diluted hydrochloric acid.
In the step 2) of the method, the Knoevenagel reaction conditions are that chloroform is used as a solvent, pyridine is used as an acid-binding agent, the molar ratio of the compound shown as the formula B to the receptor unit A is 1:5, and the reflux reaction is carried out at the temperature of 60-70 ℃ for 12-24 hours.
It is a further object of the present invention to provide a photoactive layer. The photoactive layer consists of the narrow-bandgap organic acceptor photovoltaic material with the divinyl pi-bridge and a p-type electron donor, wherein the mass ratio of the p-type electron donor to the narrow-bandgap acceptor photovoltaic material with the divinyl pi-bridge is 1: 0.5-2, preferably 1: 1.5;
the p-type electron donor is preferably a p-type conjugated polymer donor such as PTB7-Th shown in the following formula;
the photoactive layer can be mixed by adopting at least one solvent of toluene, xylene, trimethylbenzene, chloroform, chlorobenzene, dichlorobenzene and trichlorobenzene, the concentration of the narrow bandgap acceptor in the obtained mixed solution can be 0.5-50 mg/mL, preferably 4-20 mg/mL, and the concentration of the p-type electron donor can be 0.5-50 mg/mL, preferably 3-20 mg/mL.
The invention also provides an organic/polymer solar cell device comprising a first electrode, a second electrode spaced apart from the first electrode, and at least one semiconductor layer disposed between the first and second electrodes, the semiconductor layer comprising the electron acceptor (the narrow bandgap organic acceptor photovoltaic material with a divinyl pi-bridge of formula I) or the photoactive layer.
The use of said electron acceptor or said photoactive layer for the preparation of the following functional optoelectronic devices also belongs to the scope of protection of the present invention: thin film semiconductor devices, photodetection devices, single junction and stacked organic/polymer solar cell devices, and other related optoelectronic devices.
The invention provides a divinyl pi-bridge-containing narrow-bandgap organic acceptor photovoltaic material, a preparation method and application thereof in an organic/polymer solar cell and a light detection device.
Drawings
FIG. 1 shows the absorption spectra of the receptor molecule BTPV-4F prepared in example 1 of the present invention in chloroform solution and thin film.
FIG. 2 is a cyclic voltammogram of the receptor molecule BTPV-4F prepared in example 1 of the present invention.
FIG. 3 is a J-V curve of a polymer solar cell device prepared by blending the receptor molecule BTPV-4F prepared in example 1 of the invention and PTB 7-Th.
FIG. 4 is an EQE curve of a polymer solar cell device made by blending the receptor molecule BTPV-4F prepared in example 1 of the present invention and PTB 7-Th.
FIG. 5 is a J-V curve of a polymer solar cell device made by blending the receptor molecules BATPV-4F and PTB 7-Th.
Detailed Description
The experimental procedures used in the following examples are all conventional procedures unless otherwise specified.
Materials, reagents and the like used in the following examples are commercially available unless otherwise specified.
In the following examples, efforts are made to ensure accuracy with respect to numbers used (including amounts, temperature, reaction time, etc.) but some experimental errors and deviations should be accounted for. The pressures used in the following examples are at or near atmospheric pressure. All solvents used were purchased as HPLC grade and all reactions were carried out under an inert atmosphere of argon, all reagents and starting materials being commercially available unless otherwise indicated.
The PTB7-Th used in the following examples has the following structural formula, available from One Material company:
example 1 Synthesis of narrow band gap acceptor molecule BTPV-4F
The reaction was carried out according to the above reaction equation, taking 0.2mmol of BTP-CHO (from Shenzhen Rui Bing Co.), 0.6mmol of sodium hydride and 0.22mmol of tributyl (1, 3-dioxan-2-ylmethyl) phosphonium bromide, dissolving in tetrahydrofuran (20mL), evacuating the air with argon for 5 minutes, stirring at room temperature for 20 hours, quenching the reaction with 10% diluted hydrochloric acid and continuing stirring for 5 hours. The reaction solution was poured into distilled water, extracted three times with dichloromethane, dried over anhydrous magnesium sulfate and spin-dried. The crude product was purified by column chromatography using dichloromethane as eluent to yield BTPV-CHO.
Adding 0.2mmol BTPV-CHO and 1mmol 2- (5, 6-difluoro-3-oxo-2, 3-dihydro-1H-indene-1-ethylidene) malononitrile into a two-neck bottle, dissolving in 30ml chloroform, flushing with nitrogen for protection, adding 0.5ml pyridine, stirring the reaction solution at 65 ℃ for 12 hours, pouring methanol after the reaction is finished, filtering to obtain a crude product, purifying the crude product by column chromatography, and purifying the crude product with a solvent of twoMethyl chloride is used as eluent to obtain BTPV-4F. (1H NMR(300MHz,CDCl3):δ(p.p.m.) 8.70–8.43(m,6H),7.78–7.62(m,4H),4.67(d,J＝8.0Hz,4H),3.02(t,J＝7.8Hz,4H),2.09(s, 2H),1.91-1.79(m,4H),0.52–1.51(m,66H).HRMS(TOF)m/z calcd.for[M]+C86H90F4N8O2S5 1502.5726,found 1503.5757.)
The narrow band gap receptor molecule BATPV-4F with triazole as the central A' unit can be obtained by the same synthesis method, and the structural formula is shown as follows.
EXAMPLE 2 measurement of optical band gap of BTPV-4F Using absorption Spectroscopy
The absorption spectrum of the receptor BTPV-4F prepared in example 1 measured under a chloroform solution and a thin film is shown in FIG. 1. The optical band gap of the molecule can be represented by the empirical formula (E)g＝1240/λAbsorption edge) Calculated and shown in table 1.
TABLE 1 optical absorption data of the receptor BTPV-4F
| Molecule | λmax(nm) | λedge(nm) | Eg opt(eV) |
| BTPV-4F | 887 | 1021 | 1.21 |
Example 3 the electron energy level of the acceptor molecule BTPV-4F was determined using electrochemical cyclic voltammetry.
The receptor molecule BTPV-4F (0.5mg) prepared in example 1 was dissolved in 1mL of chloroform, and then the solution was dropped onto a working electrode such as a platinum plate and dried; taking 0.1mol/L acetonitrile solution of tetrabutylammonium hexafluorophosphate as electrolyte; taking a platinum wire as a counter electrode; the Highest Occupied Molecular Orbital (HOMO) and Lowest Unoccupied Molecular Orbital (LUMO) of the polymer were determined using Ag/AgCl as a reference electrode. The cyclic voltammogram of the receptor molecule BTPV-4F prepared in example 1 of the present invention is shown in FIG. 2. The HOMO and LUMO of the receptor molecule BTPV-4F prepared in the embodiment 1 of the invention are-5.39 eV and-4.08 eV respectively. The appropriate molecular energy level of the receptor molecule BTPV-4F prepared in the embodiment 1 ensures that the receptor molecule BTPV-4F can be used as a receptor photovoltaic material in an organic/polymer solar cell.
Example 4 preparation of Polymer solar cell devices of conventional construction testing of the photovoltaic performance of the narrow bandgap Acceptor photovoltaic materials of the invention
The acceptor molecule BTPV-4F or BATPV-4F prepared in example 1 of the present invention and a polymer donor PTB7-Th (molecular structure shown in FIG. 1) were blended and dissolved in chloroform at a donor/acceptor weight ratio of 1:1.5 to prepare a 16g/L blended active layer solution. A polymer solar cell device was prepared on a transparent Indium Tin Oxide (ITO) conductive glass substrate. A commonly used anode modification layer of poly (3, 4-ethylenedioxythiophene): polystyrene sulfonate (PEDOT: PSS) is coated on the surface of the ITO in a spinning mode for modification, and the thickness of the PEDOT: PSS layer is tested to be 30nm by using a Dektak XT film thickness tester. The blended active layer solution described above was then spin coated to prepare an active layer film. Then at about 10-4And (3) successively evaporating the electrode thin layers of calcium and aluminum under the pressure of Pa to obtain the polymer photovoltaic device with the conventional structure. AAA grade solar simulator AM1.5G (100 mW/cm) was used in a glove box under nitrogen atmosphere2) The open-circuit voltage, the short-circuit current, the fill factor and the energy conversion efficiency of the prepared polymer solar cell device are tested under the intensity of the voltage.
The current density-voltage curve based on BTPV-4F after the test is shown in fig. 3, and the external quantum efficiency is shown in fig. 4. The open-circuit voltage of the corresponding polymer solar cell device is 0.65V, and the short-circuit current is 22.57mA/cm2The fill factor was 65.2% and the energy conversion efficiency was 9.54%. The EQE response range is 300-1100nm, and the integrated current is 22.35 mA/cm2。
The current density-voltage curve based on BTAPV-4F after the test is shown in FIG. 5. The open-circuit voltage of the corresponding polymer solar cell device is 0.66V, and the short-circuit current is 9.89mA/cm2The fill factor was 52.3%.
TABLE 2 Polymer solar cell devices based on PTB7-Th BTPV-4F and PTB7-Th BATPV-4F at AM1.5G, 100mW/cm2Photovoltaic performance parameters under light conditions
The invention is described with reference to specific embodiments and examples. However, the present invention is not limited to only the above-described embodiments and examples. One of ordinary skill in the art will recognize, based on the teachings of this patent, that many substitutions and alterations can be made without departing from the scope of the invention, which is defined by the claims.
Claims (10)
1. A compound having the structural formula I:
the compound shown in the formula I is a compound shown in any one of the following formulas:
2. a process for preparing a compound of claim 1 comprising the steps of:
1) under the protection of inert gas, the compound shown in the formula A, tributyl (1, 3-dioxane-2-ylmethyl) phosphorus bromide and sodium hydride are subjected to a phosphorus ylide reaction to obtain a compound shown in the formula B:
in the formula A, DA' D is as defined in formula I; in the formula B, DA' D is as defined in the formula A;
2) carrying out Knoevenagel reaction on the compound shown in the formula B and the receptor unit A to obtain a compound shown in a formula I;
wherein the acceptor unit A is selected from the following:
wherein R is4Is selected from F.
3. The method of claim 2, wherein: in the step 1), the conditions of the phosphorus ylide reaction are as follows: the solvent is ultra-dry tetrahydrofuran, the adding amount of tributyl (1, 3-dioxane-2-ylmethyl) phosphorus bromide and sodium hydride is 2-5 times of the molar amount of the compound shown in the formula A, the mixture is stirred for 12-36 hours at normal temperature, and after the reaction is finished, the redundant sodium hydride is quenched by 5% diluted hydrochloric acid.
4. The method of claim 2, wherein: in the step 2), the conditions of the Knoevenagel reaction are as follows: chloroform as solvent, pyridine as acid-binding agent, and the compound shown in formula B and the acceptor unit A in a molar ratio of 1:5, and refluxing at 60-70 deg.C for 12-24 hr.
5. A photoactive layer, which consists of a compound shown in the formula I in claim 1 and a p-type electron donor, wherein the mass ratio of the p-type electron donor to the compound shown in the formula I in claim 1 is 1: 0.5-2.
6. The photoactive layer of claim 5, wherein: the p-type electron donor is a p-type conjugated polymer donor.
7. The photoactive layer of claim 6, wherein: the p-type conjugated polymer donor is PTB7-Th shown in the following formula:
8. the photoactive layer of claim 5, wherein: the photoactive layer is mixed by at least one solvent of toluene, xylene, trimethylbenzene, chloroform, chlorobenzene, dichlorobenzene and trichlorobenzene, and the concentration of the compound shown in the formula I in claim 1 in the obtained mixed solution is 0.5 mg/mL-50 mg/mL, and the concentration of the p-type electron donor is 0.5 mg/mL-50 mg/mL.
9. Use of a compound according to claim 1 or a photoactive layer according to any one of claims 5 to 8 in the preparation of a device comprising: thin film semiconductor devices, photodetection devices, single junction and stacked organic/polymer solar cell devices, and other related optoelectronic devices.
10. An organic/polymer solar cell device comprising a first electrode, a second electrode spaced apart from the first electrode, and at least one semiconductor layer disposed between the first and second electrodes, the semiconductor layer comprising a compound of formula I as claimed in claim 1 or a photoactive layer as claimed in any one of claims 5 to 8.
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| WO2024115329A1 (en) | 2022-11-28 | 2024-06-06 | Cambridge Display Technology Limited | Compounds useful in the preparation of photoresponsive device |
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